“We’re just going to start walking, followed by a full on sprint, and before you know it, you’ll be kicking your legs against the air, 3,000 feet above the ground.” I feel like that’s probably how a lot of Wilbur and Orville Wright’s conversations began just moments before attempting any number of their flights. That’s probably not a conversation you’ve ever imagined having, right? Yet lo and behold, there I was, on the last day of my twenties on the island of Maui, just below Mt. Haleakala, hearing those very words from my pilot Dexter. I stood there waiting for knots in my stomach to well up and tighten, since I get butterflies at the smallest things, be it seeing a state trooper in my rear view mirror or talking to a girl I like. Yet they never came. One moment we’re sitting on the grass talking about the virtues of Aloha spirit, and the next, just as Dexter described it, I’m kicking my legs in the air, 3,000 feet above Maui’s Upcountry.

What’s the most resilient parasite? An idea. A single idea from the human mind can build cities. An idea can transform the world and rewrite all the rules. – Inception

The thought of paragliding had never even crossed my mind. It, like most things I’ve done, began with an idea. One minute I’m hearing about it from my friend and Maui expert Wendy, and the next I’m on the phone with Dexter of Proflyght Paragliding, booking a 3,000-foot tandem paragliding flight for the last day of my twenties. While some people may have had questions about flight experience, track records, or safety, I had bigger fish to fry as I was on the phone with Dexter. “When you say ‘shoes that you can run in,’ does that include Chuck Taylors?”

Unless you’re a local, you’re likely going to be coming to Proflyght’s flight park from at least an hour away, if not longer, since it’s located in Upcountry Maui, just below Mt. Haleakala. But don’t give yourself just enough time to make your flight, but plenty of time to make a day of it and experience Upcountry Maui. Maui’s Upcountry is one of my favorite parts of the island because you get to experience a more local vibe than you’ll find in the resort towns. If you’re lucky, you may reach the top of Maui’s Upcountry as the sun is rising over the ocean. Since your flight time will likely be early in the morning, start off with at least a cup of coffee, if not a snack too, at Grandma’s Maui Coffee, which is a renowned coffee shop and just 10-15 minutes from the flight park. Afterward, head to Maui’s only winery for wine tasting (Don’t go expecting Napa wine) and have lunch at Kula Bistro (Go for the crab cake panini).

Paragliding over upcountry MauiUpon arriving, you’ll be greeted by instructors at the landing pad, who will take your payment (Cash or credit), give you a couple pages of paperwork to fill out, and a brief overview of the flight. While you can back out once on top of the mountain, let’s be honest, once you hand over your paper or plastic, you’re in it to win it. From there, it’s a 10-minute steep, curvy ride to the top of the hill. I talked with Dexter and some of the other instructors about the paragliding sport and their loves for both it and the island of Maui, since all of the instructors had moved to Maui from the mainland. Once at the top, you have plenty of opportunities to take some photos of the landscape and of yourself getting suited up. It can take some time to unpack the glider, suit up, and go over safety and instruction before actual lift off.

After instructions from Dexter about the basics of flying, I was suited up and locked in, ready to run down the mountain and in the words of Seal, fly like an eagle. But it’s in this way that paragliding is like surfing. Like waiting for the right wave to paddle and catch, with paragliding you wait for the right wind conditions. This could be mere seconds or minutes, depending on the wind conditions. For us it was about 15 minutes, during which time Dexter and I talked about my fondness for the Aloha spirit. We started with a slow walk until I felt the resistance of the parachute behind me. It was then just several seconds of sprinting down the hill and then all of a sudden I was kicking my feet in the air like I was Fred Flintstone driving the footmobile off a cliff.

paragliding in hawaii

Maui Hawaii rainbow

I’ve done a few adventure sports in my life, such as surfing, parasailing, rock climbing, and ziplining, but none have brought with it such feelings of being carefree and bliss as paragliding over Maui did. One moment I was running as fast as I could down a hill and the next I was kicking back, manipulating the turns of the glider with my arms, while flying over treetops, lavender farms, and even a full circle rainbow. I gripped tightly to my iPhone as I took photos of the countryside and coastline that I wouldn’t see like that again. As cheesy as it sounds to say, I indeed was flying like an eagle. There really was a serenity to flying above the rolling hills, farmland, and treetops that even now, I find hard to put into words. Minutes later we came in for what was a soft landing and without even taking the time to get unstrapped or take off my helmet, I was giving high fives and asking Dexter what the process was for taking solo lessons.

Paragliding above Maui, HawaiiShortly upon landing, I immediately reflected on my 20s and what that experience on the last day of my 20s meant. The first three-fourths of my 20s were rather ordinary and what many would probably call normal. Yet I wasn’t comfortable in my own skin. It felt like there was this wonder and beauty to the world that was out there, yet something that was elusive, always just short of my grasp. So I figuratively strapped on a parachute, got a running head start, and jumped. I feel like I’ve been flying ever since. Paragliding that day over Maui was the exclamation point on my 20s. I may have limped through most of my 20s, but I was flying high out of them and into my 30s. It was on that hilltop that the idea of my 30 at 30 list was conceived. If the first of 30 new experiences was any indication, year 30 will be pretty fly.

Know Before You Go

  • Prices are $185 for the 3,000-foot descent and $95 for the 1,000-foot descent. I highly recommend the 3,000-foot descent. While you’re up in the air for 10-15 minutes, it feels like no time, and if you’re like me,  you’ll want to immediately go back and do it all over again.
  • Bring either cash or a credit card.
  • Wear shoes you can run in. In other words, don’t wear flip flops or Uggs. While Chuck Taylors may suffice, I recommend some running shoes.
  • Wear long sleeves and bring a jacket to be on the safe side. I was fine with long pants and a long sleeve shirt, but have a lightweight jacket on hand in case you need it. It’s a little cooler in Upcountry Maui than it is along the coast.
  • If you bring a camera or iphone, make sure it has a strap. You can take photos while up in the air, but make sure it’s strapped to your hand, as you aren’t likely to find it (Or find it in one piece) if it drops out of your hand from 3,000 feet in the air.